This invention relates to novel pyridine sulfonylurea herbicidal compounds, agriculturally suitable compositions thereof and a method of using them to control the growth of undesired vegetation.
New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.
The "sulfonylurea" herbicides are an extremely potent class of herbicides discovered within the last few years. A multitude of structural variations exist within this class of herbicides, but they generally consist of a sulfonylurea bridge, --SO.sub.2 NHCONH--, linking two aromatic or heteroaromatic rings.
U.S. Pat. Nos. 4,579,583 and 4,690,707 disclose herbicidal pyridinesulfonylureas of the formula ##STR1## wherein XA is NR.sub.6 R.sub.7 ; and
R.sub.6 and R.sub.7 are independently H, C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.6 alkenyl, C.sub.3 -C.sub.6 alkynyl, C.sub.3 -C.sub.6 alkoxyalkyl, C.sub.1 -C.sub.4 cyanoalkyl, or taken together form a 5- or 6-membered heterocyclic ring which may also contain O, S, SO or NR.sub.8. PA1 R.sub.2 is H, Cl, Br or CH.sub.3. PA1 R.sub.1 is NH(C.sub.1 -C.sub.4)alkyl or N(C.sub.1 -C.sub.4 alkyl).sub.2. PA1 R.sub.1 is NH.sub.2, NH(C.sub.1 -C.sub.4)alkyl or N(C.sub.1 -C.sub.4 alkyl).sub.2. PA1 R is H or CH.sub.3 ; PA1 R.sub.1 is H, F, Cl, Br, I, CN, C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 haloalkyl, OCH.sub.3, OCH.sub.2 CH.sub.3, OCH.sub.2 CF.sub.3, OCF.sub.2 H, SCH.sub.3, SCF.sub.2 H, C.sub.1 -C.sub.3 alkylsulfonyl or SO.sub.2 CF.sub.2 H; PA1 R.sub.2 is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.2 haloalkyl, CN, OH, C.sub.1 -C.sub.2 alkoxy, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, C.sub.1 -C.sub.2 alkyl substituted by CN, C.sub.1 -C.sub.2 alkoxy or C.sub.1 -C.sub.2 alkylthio, C.sub.3 -C.sub.4 cycloalkyl, C.sub.3 -C.sub.4 alkenyl, C.sub.3 -C.sub.4 alkynyl or C(O)R.sub.5 ; PA1 R.sub.3 is H, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.2 haloalkyl; or PA1 R.sub.2 and R.sub.3 may be taken together as --(CH.sub.2).sub.n -- or ##STR6## R.sub.4 is H, F, Cl or CH.sub.3 ; R.sub.5 is H, C.sub.1 -C.sub.3 alkyl, C.sub.1 -C.sub.2 alkoxy, NH.sub.2, NHCH.sub.3 or N(CH.sub.3).sub.2 ; PA1 R.sub.6 is H, C.sub.1 -C.sub.2 alkyl or phenyl; PA1 R.sub.7 is H or CH.sub.3 ; PA1 n is 2, 3, 4 or 5; PA1 p is 0 or 1; ##STR7## X is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkyl, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, halogen, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino or di(C.sub.1 -C.sub.3 alkyl)amino; PA1 Y is H, C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 haloalkoxy, C.sub.1 -C.sub.4 haloalkylthio, C.sub.1 -C.sub.4 alkylthio, C.sub.2 -C.sub.5 alkoxyalkyl, C.sub.2 -C.sub.5 alkoxyalkoxy, amino, C.sub.1 -C.sub.3 alkylamino, di(C.sub.1 -C.sub.3 alkyl)amino, C.sub.3 -C.sub.4 alkenyloxy, C.sub.3 -C.sub.4 alkynyloxy, C.sub.2 -C.sub.5 alkylthioalkyl, C.sub.2 -C.sub.5 alkylsulfinylalkyl, C.sub.2 -C.sub.5 alkylsulfonylalkyl, C.sub.1 -C.sub.4 haloalkyl, C.sub.2 -C.sub.4 alkynyl, C.sub.3 -C.sub.5 cycloalkyl, azido, cyano, ##STR8## or N(OCH.sub.3)CH.sub.3 ; m is 2 or 3; PA1 Q.sub.1 and Q.sub.2 are independently O or S; PA1 R.sub.a is H or C.sub.1 -C.sub.3 alkyl; PA1 R.sub.b and R.sub.c are independently C.sub.1 -C.sub.3 alkyl; PA1 Z is CH, N, CCH.sub.3, CC.sub.2 H.sub.5, CCl or CBr; PA1 Y.sub.1 is O or CH.sub.2 ; PA1 X.sub.1 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or OCF.sub.2 H; PA1 X.sub.2 is CH.sub.3, C.sub.2 H.sub.5 or CH.sub.2 CF.sub.3 ; PA1 Y.sub.2 is OCH.sub.3, OC.sub.2 H.sub.5, SCH.sub.3, SC.sub.2 H.sub.5, CH.sub.3 or CH.sub.2 CH.sub.3 ; PA1 X.sub.3 is CH.sub.3 or OCH.sub.3 ; PA1 Y.sub.3 is H or CH.sub.3 ; PA1 X.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3 or Cl; and PA1 Y.sub.4 is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5 or Cl; PA1 (1) when X is halogen, then Z is CH and Y is OCH.sub.3, OC.sub.2 H.sub.5, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, OCF.sub.2 H, OCF.sub.2 Br or N(OCH.sub.3)CH.sub.3 ; PA1 (2) when X and/or Y is C.sub.1 haloalkoxy, then Z is CH; PA1 (3) when W is S, then R is H, A is A-1, Z is CH or N, and Y is CH.sub.3, OCH.sub.3, OC.sub.2 H.sub.5, CH.sub.2 OCH.sub.3, C.sub.2 H.sub.5, CF.sub.3, SCH.sub.3, OCH.sub.2 CH.dbd.CH.sub.2, OCH.sub.2 C.tbd.CH, OCH.sub.2 CH.sub.2 OCH.sub.3, CH(OCH.sub.3).sub.2 or ##STR9## (4) when the total number of carbon atoms of X and Y is greater than four, then the combined number of carbons of R.sub.2 and R.sub.3 is less than or equal to six; and PA1 (5) X.sub.4 and Y.sub.4 L are not simultaneously Cl. PA1 1. Compounds of Formula I wherein R.sub.4 is H; PA1 2. Compounds of Preferred 1 wherein R.sub.2 is C.sub.1 -C.sub.2 haloalkyl, OH, C.sub.1 -C.sub.2 alkoxy, NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2, C.sub.1 -C.sub.2 alkyl substituted by C.sub.1 -C.sub.2 alkylthio, C.sub.3 -C.sub.4 cycloalkyl or C(O)R.sub.5 ; PA1 3. Compounds of Preferred 2 wherein PA1 4. Compounds of Preferred 3 wherein PA1 5. Compounds of Preferred 4 wherein PA1 6. Compounds of Preferred 5 wherein PA1 7. Compounds of Preferred 1 wherein PA1 8. Compounds of Preferred 7 wherein PA1 9. Compounds of Preferred 8 wherein PA1 10. Compounds of Preferred 9 wherein PA1 11. Compounds of Preferred 10 wherein PA1 12. Compounds of Formula I wherein PA1 13. Compounds of Preferred 12 wherein PA1 14. Compounds of Preferred 13 wherein PA1 15. Compounds of Preferred 14 wherein PA1 16. Compounds of Preferred 15 wherein PA1 17. Compounds of Preferred 16 wherein PA1 18. Compounds of Preferred 12 wherein PA1 19. Compounds of Preferred 18 wherein PA1 20. Compounds of Preferred 19 wherein PA1 21. Compounds of Preferred 20 wherein PA1 22. Compounds of Preferred 21 wherein PA1 X.sub.5 is Cl, NH.sub.2 or NHC(CH.sub.3).sub.3 ; PA1 R.sub.1 is H, R.sub.3 is H, R.sub.4 is H, p is O and X.sub.5 is NH.sub.2, then PA1 R.sub.2 is other than H. PA1 L is a leaving group such as Cl, Br, I, alkyl sulfide, etc.; PA1 L is as previously defined.
U.S. Pat. No. 4,544,401 discloses herbicidal pyridine sulfonylureas of the formula ##STR2## wherein R.sub.1 is NR.sub.6 R.sub.7 ; and
EP-A-101,670 discloses a process for the preparation of herbicidal sulfonylureas of the formula ##STR3## wherein A is --C.dbd.N--; and
U.S. Pat. No. 4,518,776 discloses a process for the preparation of herbicidal sulfonylureas of the formula ##STR4## wherein A is --C.dbd.N--; and